Based on your post I'm going to suggest looking into some REIT (Real Estate Investment Trust) funds.

This is not without issues (the biggest of which is getting more funds into the IRA/LLC after future contributions), but it is worth exploring if it might be a good fit for you.On the other hand, if you are not looking for as much control, I have a great deal of respect for Quest Trust Company and it's owner Quincy Long.  

Shaking the trees for rent is work, trust me. 

How would you recommend us going about finding a contractor we can trust?

I use Carter Bank & Trust in Fayetteville.

The applicant is trying to get you to trust them and is appealing to your greed. 

I'd trust a PM or realtor with market knowledge of the local area over internet rental estimator sites.

@Charles ElliottI don’t remember who said this, but I’ve heard this on BP many times over, “Cashflow keeps you in the game, equity builds you wealth.”My vote is for holding onto the property if you find the numbers work for you and find someone you trust to manage the property.

I'm wondering if I should be buying the investment properties under my Living Trust in order to avoid probate issues in future OR rather my own name. 

I used Builders Trust Capital to cash out with all my rental properties in the past, I had such a good relationship with them I now actually work for them in addition to growing my portfolio.